Synthesis and properties of new photoactivable derivatives of tetrodotoxin.
The Pfitzner-Moffatt oxidation procedure has been used to prepare two new photoactivable derivatives of tetrodotoxin that have been synthesized with high specific radioactivities (17.5 Ci/mmol and 30 Ci/mmol). They specifically bind to axonal membranes with affinities of 5.2-14.2 nM. They dissociate from their membrane complex with half-lives of 10.8 and 20 min. In the dark, these compounds give a reversible block of the sodium channels. After ultraviolet irradiation, they induce an irreversible blockade of the nerve channels.
D000818:Animals; D001369:Axons / Q000378:metabolism; D001681:Biological Assay; D003386:Brachyura; D002462:Cell Membrane / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D005029:Ethylenediamines; D007700:Kinetics; D008239:Lysine; D010777:Photochemistry; D013329:Structure-Activity Relationship; D013779:Tetrodotoxin / Q000378:metabolism / Q000494:pharmacology
D005029:Ethylenediamines; D013779:Tetrodotoxin; D008239:Lysine